[ CAS No. 161601-29-2 ] {[proInfo.proName]}

Name: 161601-29-2|(1S,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid|95%
Brand: Ambeed
SKU: A897887
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Quality Control of [ 161601-29-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 161601-29-2 ]

CAS No. :	161601-29-2	MDL No. :	MFCD02259726
Formula :	C₁₁H₁₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RNJQBGXOSAQQDG-YUMQZZPRSA-N
M.W :	229.27	Pubchem ID :	1512528
Synonyms :

Safety of [ 161601-29-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 161601-29-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 161601-29-2 ]

[ 161601-29-2 ] Synthesis Path-Downstream 1~26

1
[ 161601-29-2 ]
C₃₂H₃₇F₇N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The hydrochloric acid salt intermediate of example 1 step E (50mg, O.lOmmol) was suspended in 2mL DCM followed by the addition of 52mg of diisopropylethyl amine (0.40mmol). After 5 minutes, (l£,3S)-3-[(/ert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (34mg, 0.15mmol), EDC (38mg, 0.20mmol) and DMAP (3mg, 0.02mmol) were added. The workup and purification followed the procedure for example 3 step A. This provided the title compound. 1H-NMR (CD3OD): δ 1.30-1.36 (m,3H), 1.38-1.50 (m, 9H), 1.70-2.15 (m, 4H), 2.36-2.48 (m, IH), 2.56-2.78 (m, 3H), 3.16-3.28 (m, 2H), 3.60-3.70 (m, IH), 3.90-4.04 (m, 2H), 4.16-4.44 (m, IH), 4.64-4.78 (m, 2H), 6.86-6.94 (m, 2H), 7.06- 7.16 (m, 2H), 7.44 (s, 2H), 7.77 (s, IH) ppm. MS: (MHy55 591.

Reference： [1]Patent: WO2006/73589,2006,A2 .Location in patent: Page/Page column 25

2
[ 161601-29-2 ]
[ 613-92-3 ]
tert-butyl {(1S,3S)-3-[([(1Z)-amino(phenyl)methylene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;	EXAMPLE 7; A^-[(l1S',3iS,)-3-(3-phenyl-l,2,4-oxadiazol-5-yl)cyclopentyl]-l//-pyrazolo[3,4-</]pyrimidin-4-amine; Step A: terf-butyl {(1S,3S>3-[([(1Z)-amino(phenyl)methylene]amino}oxy)carbonyl]cyclopentyl}carbamate; To a solution of (lS^S^-Kte^butoxycarbonytyaminoJcyclopentanecarboxylic acid (200 mg, 0.872 mmol) in methylene chloride (10 mL) at room temperature was added HOBt (134 mg, 0.872 mmol), EDC (189 mg, 0.916 mmol) and 7V-hydroxybenzenecarboximidamide (131 mg, 0.960 mmol). After 3 h, the reaction was poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (30% ethyl acetate / hexanes -> 100% ethyl acetate / hexanes) gave the title compound (277 mg) as a white solid. MS 348 (M+l); 'HNMR(300 MHz, DMSO-4): 7.71-7.68 (m, 2H), 7.50-7.41 (m, 3H), 6.91 (d, J= 6.6 Hz, 1H), 6.75 (s, 2H), 3.88 (m, 1H), 3.12-3.07 (m, 1H), 2.05-L43 (m, 6H), 1.32 (s, 9H).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 44

3
[ 161601-29-2 ]
[ 875898-17-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 5; Af-[(15,35)-3-(4-benzyl-l,3-oxazol-2-yl)cyclopentyl]-l//-pyrazolo[3,4-<^]pyrimidin-4-amine; Step A: tert-buty [(l1S',3<S)-3-(aminocarbonyl)cyclopentyl]carbamate; To a solution of (l^iS^-f^e^butoxycarbony^aminoJcyclopentanecarboxylic acid (480 mg, 2.09 mmol) and HOBt (849 mg, 6.28 mmol) in DMF (6 mL) at room temperature was added EDC (1.20 g, 6.28 mmol). After 30 minutes, ammonium hydroxide (1.3 mL) was added to the reaction. After 72 h, the reaction was poured into ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated to give the title compound (306 mg) as a white solid. This material was sufficiently pure for the next step. 'H NMR (400 MHz, DMSCW6): 7.20 (s, 1H), 6.81 (d,y= 8.0 Hz, 1H), 6.67 (s, 1H), 3.82-3.80 (m, 1H), 2.69-2.64 (m, 1H), 1.89-1.76 (m, 3H), 1.61-1.52 (m, 2H), 1.37 (s,9H).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 39

4
[ 161601-29-2 ]
[ 74-89-5 ]
[ 875899-15-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 50; A^-[(l,S',3lS)-3-(5-benzyl-4-methyl-47/-l,2,4-triazol-3-yl)cyclopentyl]-l//-pyrazolo[3,4-(^]pyrimidin-4-amine; Step A: ter/-butyl {(lS,3S)-3-[(methylamino)carbonyl]cyclopentyl}carbamate; To a solution of (lS^^-S-lXtert-butoxycarbonyOaminojcyclopentanecarboxylic acid (0.910 g, 3.95 mmol) and HOBt (1.21 g, 7.90 mmol) in anhydrous DMF (20 mL) at room temperature under N2 was added EDC (1.52 g, 7.90 mmol). After 60 minutes, 2.0 M methylamine in THF (0.430 mL, 11.9 mmol) was added to the reaction. After 14 hours, the reaction was poured into ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated to give the title compound (0.95 g) as a white solid. This material was sufficiently pure for the next step. MS 485.4 (2M+1) and 187.3 (M-55).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 89

5
[ 875898-62-7 ]
[ 161601-29-2 ]
tert-butyl {(1S,3S)-3-[([(1Z)-1-amino-2-hydroxy-2-phenyl-ethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step C; ter/-Butyl {(lS,35)-3-[([(lZ)-l-amino-2-hydroxy-2-phenyl-ethylidene]amino}oxy) carbony l]cyclopentyl} carbamate; To a solution of (l£,3S)-3-[(ter/-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1.0 g, 4.4 mmol) in methylene chloride (50 mL) at room temperature was added HOBt (0.70 g, 4.6 mmol), and EDC (0.92 g, 4.8 mmol). After 20 minutes, (lZ)-N-hydroxy-2-phenyl-2-(tetrahydro-2//-pyran-2-yloxy)ethanimidamide (1.8 g, 7.4 mmol) was added to the reaction. After 14 hours, the reaction was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give the title compound (0.30 g) as a waxy solid. HRMS (M+ff): calculated = 378.2024, observed = 378.2042.

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 56-57

6
[ 876042-93-2 ]
[ 161601-29-2 ]
tert-butyl {(1S,3S)-3-[([(1Z)-1-amino-2,2-difluoro-2-phenylethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step D: tert-butyl {(l<S',31S)-3-[([(lZ)-l-amino-2,2-difluoro-2-phenylethyIidene]amino}oxy) carbonyl]cyclopentyl} carbamate; To a solution of (liS',35)-3-[(/eA-/-butoxycarbonyl)amino]cyclopentanecarboxylic acid (0.17 g, 0.76 mmol) in methylene chloride (20 mL) at room temperature was added HOBt (0.13 g, 0.86 mmol) and EDC (0.16 g, 0.82 mmol). After 20 minutes, (lZ)-2,2-difiuoro-JV-hydroxy-2-phenylethanimidamide (0.14 g, 0.75 mmol) was added to the reaction. The reaction was permitted to stir at room temperature overnight. The reaction was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give the title compound (0.274 g) as a solid. HRMS (M+tT): calculated = 398.1886, observed = 398.1886.

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 63

7
[ 161601-29-2 ]
[ 876032-39-2 ]
tert-butyl {(1S,3S)-3-[([(1Z)-1-amino-2-(4-methylphenyl)-2-(tetrahydro-2H-pyran-2-yloxy)ethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step D: tert-Buty] {(15,35)-3-[([(lZ)-l-amino-2-(4-methylphenyl)-2-(tetrahydro-2//-pyran-2-yloxy)ethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate; To a solution of (15',35)-3-[(?er?-butoxycarbonyl)amino]cyclopentanecarboxylic acid (275 mg, 1.20 mmol) in methylene chloride (10 mL) at room temperature was added HOBt (193 mg, 1.26 mmol), and EDC (253 mg, 1.32 mmol). After 15 minutes, (lZ)-7V-hydroxy-2-(4-methylphenyl)-2-(tetrahydro-2//-pyran-2-yloxy)ethanimidamide (412 mg, 1.56 mmol) was added to the reaction. After 1.6 hours, the reaction was poured into saturated sodium bicarbonate solution and extracted with methylene chloride. The combined organic layers were washed with 1M sodium hydroxide, dried over sodium sulfate, filtered and concentrated to give the title compound (570 mg) as a solid. MS 476 (M+l).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 67

8
[ 876043-03-7 ]
[ 161601-29-2 ]
tert-butyl {(1S,3S)-3-[([(1Z)-1-amino-2,2-difluoro-2-(4-methylphenyl)ethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		StepD: tert-butyl {(lS',35)-3-[([(lZ)-l-amino-2,2-difluoro-2-(4-methylphenyl)ethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate; To a solution of (15',35)-3-[(/e7"/-butoxycarbonyl)amino]cyclopentanecarboxylic acid (425 mg, 1.85 mmol) in methylene chloride (5 mL) at room temperature was added HOBt (250 mg, 1.85 mmol), and EDC (355 mg, 1.85 mmol). After 40 minutes, (lZ)-2,2-difluoro-A^-hydroxy-2-(4-methylphenyl)ethanimidamide (371 mg, 1.85 mmol) was added to the reaction. After 8 hours, the reaction was poured into saturated sodium bicarbonate solution and extracted with methylene chloride. The combined organic layers were washed with 1M sodium hydroxide, dried over sodium sulfate, filtered and concentrated to give the title compound (600 mg) as a waxy solid. MS 362 (M+l).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 72

9
[ 161601-29-2 ]
[ 57676-54-7 ]
[ 875899-03-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step B: ter/-butyl [(15,35)-3-({2-[(4-methylphenyl)acetyl]hydrazino}carbonyl)cyclopentyl]carbamate; A mixture of (15,35)-3-[(/e^butoxycarbonyl)amino]cyclopentanecarboxylic acid (1.10 g, 4.80 mmol), HOBt (0.78 g, 5.07 mmol), and EDC (0.97 g, 5.07 mmol) in methylene chloride (220 mL) and DMF (25 mL) was stirred at room temperature under N2. After 30 minutes, 2-(4-methylphenyl)acetohydrazide (0.80 g, 4.87mmol) was added to the reaction. After 14 hours, the gel-like mixture was poured into ethyl acetate. The organic layer was washed with 1 N sodium hydroxide, water, brine, dried over sodium sulfate, filtered and concentrated to yield the title compound (1.82 g) as a white solid. HRMS (M+Na+): calculated = 398.2050, observed = 398.2059.

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 84

10
[ 161601-29-2 ]
[ 19227-11-3 ]
tert-butyl {(1S,3S)-3-[([(1Z)-1-amino-2-phenylethylidene]amino}oxy)carbonyl]cyclopentyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		StepB; iert-butyl {(lS;3^3-[([(lZ>l-amino-2-phenylethylidene]amino}oxy)carbonyl]cyclopentyl} carbamate; To a solution of (lS,3£)-3-[(fcr/-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1.99 g, 8.68 mmol) in methylene chloride (20 mL) at room temperature was added HOBt (1.40 g, 9.11 mmol), and EDC (1.83 g, 9.55 mmol). After 40 minutes, (lZ)-./V'-hydroxy-2-phenylethanimidamide (1.70 g, 11.3 mmol) was added to the reaction. After 8 hours, the reaction was poured into saturated sodium bicarbonate solution and extracted with methylene chloride. The combined organic layers were washed with 1M sodium hydroxide, dried over sodium sulfate, filtered and concentrated to give the title compound (3.97 g) as a waxy solid. MS 362 (M+l).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 48

11
[ 161601-29-2 ]
[ 875898-42-3 ]
[ 1312774-71-2 ]

Yield	Reaction Conditions	Operation in experiment
		Step B; tert-buty {(lS,3S)-3-[([(lZ)-l-amino-2-(4-methylphenyl)ethylidene]amino}oxy)carbonyl]cyclopentyl} carbamate; To a solution of (lS^iS^-Kto-Z-butoxycarbonyOaminojcyclopentanecarboxylic acid (12.9 g, 56.1 mmol) in methylene chloride (150 mL) at room temperature was added HOBt (8.73 g, 57.0 mmol), and EDC (11.0 g, 57.2 mmol). After 20 minutes, (lZ)-iV-hydroxy-2-(4-methylphenyl)ethanimidamide (11.2 g, 68.4 mmol) was added to the reaction and the reaction was permitted to stir an addition 12 hours. The reaction was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with 1M sodium hydroxide, dried over sodium sulfate, filtered and concentrated to give the title compound (19.1 g) as a waxy solid. MS 376.3 (M+l).

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 51

12
[ 161601-29-2 ]
[ 937-39-3 ]
[ 875898-99-0 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 47; /V-[(15',35)-3-(5-benzyl-l,3,4-oxadiazol-2-yl)cyclopentyl]-l//-pyrazolo[3,4-^]pyrimidin-4-amine; Step A: tert-buty ((lS^S^-IP-tphenylacetyOhydrazinoJcarbonylJcyclopentyOcarbamate; To a solution of (lS,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentanecarboxyIic acid (0.83 g, 3.6 mmol) in methylene chloride (15 mL) was added O-benzotriazoI-1-yl-N, N, N1, N1, tetramethyluronium hexafluorophosphate (2.6 g, 5.9 mmol) at room temperature under N2. After 30 minutes, 2-phenylacetohydrazide (0.55 g, 3.7 mmol) was added and the reaction was stirred for 14 hours. The gel-like mixture was poured into ethyl acetate and the organic layer was washed with 1 N sodium hydroxide, water, brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (1% isopropanol / methylene chloride -> 15% isopropanol / methylene chloride) gave the title compound (0.89 g) as a brown solid. This material was sufficiently pure for the next step. HRMS (M+fT): calculated = 362.2075, observed = 362.2073.

Reference： [1]Patent: WO2006/17409,2006,A2 .Location in patent: Page/Page column 81

13
[ 161601-29-2 ]
[ 1201186-57-3 ]
C₂₄H₃₀N₆O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4399 - 4404

14
[ 161601-29-2 ]
C₁₆₂H₂₇₁N₃₅O₄₈ [ No CAS ]
C₁₁₈H₂₀₀N₃₆O₂₉ [ No CAS ]

Reference： [1]Patent: WO2017/218922,2017,A2 .Location in patent: Page/Page column 283

15
[ 161601-29-2 ]
C₉H₁₁ClFN [ No CAS ]
C₁₅H₂₀ClFN₂O [ No CAS ]

Reference： [1]Patent: JP2015/54844,2015,A

16
[ 161601-29-2 ]
C₉H₁₁ClFN [ No CAS ]
tert-butyl [(1S,3S)-3-[2-(2-chloro-5-fluorophenyl)propan-2- yl]carbamoyl}cyclopentyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
145.3 mg	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;	(1S,3S)-3-[(tert-butoxycarbonyl) amino] cyclopentanecarboxylic acid (120.1 mg)WSCD (102.7 mg),2- (2-chloro-5-fluorophenyl) propan-2-amine(Compound of Reference Example 7, 80.0 mg),HOBt (82.4 mg),And a solution of triethylamine (0.12 mL) in dichloromethane(3 mL) were stirred at room temperature overnight.The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography,The target compound (145.3 mg) was obtained as a solid.

Reference： [1]Patent: JP2015/54844,2015,A .Location in patent: Paragraph 0123; 0124

17
[ 161601-29-2 ]
[ 76-05-1 ]
N-(2-aminoethyl)maleimide trifluoroacetate [ No CAS ]
(1S,3S)-3-amino-N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]cyclopentanecarboxamide trifluoroacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from commercially available 5 (1S,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid and likewise commercially available trifluoroacetic acid/ 1-(2-aminoethyl)-1H-pyrrole-2,5-dione (1:1) by coupling with HATU in the presence of N,N-diisopropylethylamine and subsequent deprotection with TFA. [0938] HPLC (Method 11): Rt=0.19 min; [0939] LC-MS (Method 3): Rt=0.88 min; MS (ESIpos): m/z=250 (M-H)-.

Reference： [1]Patent: US2020/138970,2020,A1 .Location in patent: Paragraph 0936-0939

18
[ 161601-29-2 ]
[ 1159680-21-3 ]
[ 199110-64-0 ]
N-(9-fluorenylmethyloxycarbonyl)-5-hydroxy-L-tryptophan [ No CAS ]
(1S,3S)-N-((S)-1-(((S)-3-([1,1'-biphenyl]-4-yl)-1-(((S)-1-amino-6-guanidino-1-oxohexan-2-yl)amino)-1-oxopropan-2-yl)amino)-3-(5-hydroxy-1H-indol-3-yl)-1-oxopropan-2-yl)-3-aminocyclopentane-1-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 11229 - 11246

19
[ 161601-29-2 ]
[ 593-51-1 ]
[ 875899-15-3 ]

Reference： [1]Patent: WO2022/53010,2022,A1 .Location in patent: Page/Page column 248; 252

20
[ 161601-29-2 ]
(1S,3S)-3-amino-N-methylcyclopentanecarboxamide hydrochloride [ No CAS ]